


After Party

by DRHPaints



Category: American (US) Actor RPF, Bill Hader - Fandom, Bill Hader RPF, Conan O’Brien, Conan O’Brien RPF, Late Night Host RPF, US Comedians RPF
Genre: Blow Jobs, Cumplay, Cunnilingus, Dom/sub Undertones, Explicit Language, Explicit Sexual Content, Face-Fucking, Multi, One Shot, Plot What Plot/Porn Without Plot, Referenced Lesbian Sex, Threesome - F/M/M, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2020-11-03
Updated: 2020-11-03
Packaged: 2021-03-08 22:55:33
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,696
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27364633
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Bill, Conan, and Lydia are at a party that gets too rambunctious, so they slip outside to hang out by the fire pit. When Lydia recounts a tale of her sexual exploits, Bill and Conan get excited and the three of them have some fun under the moonlight.
Relationships: Bill Hader/Original Female Character/Conan O’Brien
Comments: 2
Kudos: 6





	After Party

**Author's Note:**

  * For [damn_conan](https://archiveofourown.org/users/damn_conan/gifts).



Covering her ears, Lydia stepped out onto the patio, Bill and Conan in tow as they grimaced back at the roaring festivities.

“Jeez…” Lydia shook her head as Bill closed the sliding glass doors behind them. “Who would’ve thought a release party for a comedy band album would get so rowdy?”

“Right?” Arching an eyebrow, Bill blinked. Another cheer went up inside the house and the three mutually cringed.

“Come on.” Conan suggested. “Let’s go hang out by the fire pit. Quieter.”

They moseyed across the lawn, Conan sipping on a glass of Pinot while Bill stuck to water before they came to a stop around the fire. Everyone else absorbed with the party, the noise of the cicadas could be heard far off and a salty breeze rolled in off the ocean as they stared into the crackling flames.

Chuckling, Lydia wagged her head. “As much as I wanted them to turn the music down, gotta admit, that threeway song is catchy as hell.”

Bill giggled, closing his eyes. “Yeah, who knew right?” Holding up his large palms, he shook his head. “Andy, Justin and the guys are always just trying to be silly, but they end up making legitimately great tunes.”

“Yeah, turns out mocking fragile masculinity is hilarious.” Smirking, Conan raised an almost impossibly faint orange eyebrow. “Never would’ve guessed.” He laughed and the others joined in.

“So...you guys have had one, right?” Tipping back her drink, Lydia glanced between the two of them.

Bill knit his dark eyebrows together. “Had one what?”

“A threeway.” Lydia shrugged.

Conan burst out laughing, eyes scrunched and clutching his chest. “Yeah! Right!” Recovering, he held up his freckled hands incredulously. “Who’s going to want my pasty, Gumby body in a threeway?” Lydia raised an eyebrow, saying nothing.

Giggling, Bill’s left eye slivered and his overbite exaggerated as he fell over on himself, slapping his knee. “Right? And I’m so fucking awkward. I could never…” Bill affected a warbling prepubescent voice. “Uh...ma’am...could I please engage in consensual coitus with you and your friend, if it’s not too much trouble?”

They all cackled, but once they calmed, Lydia took a drink and casually raised her shoulder. “I’ve had a couple…”

“A...a _couple?”_ Conan eyed her disbelievingly. “Seriously?”

Shrugging, Lydia merely sipped and watched the fire for a minute. Conan looked to Bill, who glanced at Lydia. “That...must’ve been...interesting…”

A slow smirk spread over her curvaceous lips and her eyebrows shot up for half a second. “You could say that.”

Grip tightening around his glass, Conan unconsciously took half a step forward. “So, um…” Chewing on his thin lips, Conan didn’t want to overstep any boundaries. But he figured he’d been friends with Lydia for years. They were close, had discussed sex before, at least in the theoretical, so it probably wasn’t that weird to ask. “So...what was it like?”

“Which time?” Lydia tossed back her mane of crimson waves. “Me and a guy with another woman, or me and a guy with another man?”

“Woman.” Bill and Conan responded in unison and Lydia folded over in laughter.

“Why am I not surprised? Alright, well…” Casting her eyes skyward, Lydia thought back. “It was my senior year of college, and my roommate Tiffany, gorgeous: petite, black hair, curvy; she was dating this guy Daniel, right? And ugh…” Grinning, Lydia shook her head. “He was so handsome. Tall, broad shoulders, jawline that could cut glass, blue eyes, funny…”

Bill was tempted to look over at Conan, but found he couldn’t tear his eyes away from Lydia as she continued in her reverie. “So we were drinking, of course…” Lydia rolled her eyes. “And Daniel started complimenting me. At first I expected Tiffany to get mad. He wasn’t saying anything really out of line, just, you know ‘you’re really pretty’ stuff like that. In the beginning. But...I don’t know, maybe they talked about it beforehand…” Tilting her head, Lydia threw back the last of her drink. “Because Tiffany caught my eye and I could tell she was like...into it. Then...Daniel he...he started talking about how much…” Sly smile crossing her face, Lydia slid her eyes away. “How much he liked my tits, you know, and, um...then...then Tiffany agrees with him…”

Going quiet, Lydia stared into the fire and Bill realized his mouth was full of saliva. Swallowing, he blinked. “Um...then...then what happened?”

Lydia gave him a curious glance, closing and opening her eyes slowly. “Well, then I asked Tiffany if she wanted to play with them…” Mouth falling open, Conan promptly shut it, hoping she didn’t catch his shocked expression. “And Tiffany came over. We took off our shirts, started kissing. Mmm…” Releasing a long, low hum, Bill felt his cock twitch below his slacks as he watched Lydia’s eyes fall shut in blissful remembrance. “She felt so good. Honestly…” Chuckling, Lydia flicked a hand away. “For a few minutes I think we forgot Daniel was there…”

“What, um…” Tongue darting over his thin lips. Conan was getting hard, knew he should stop, should change the subject, should probably even get in his Tesla and go home, but the need to hear the rest of the story was insatiable. “What do you mean?”

“Well…” Biting her lip, Lydia looked up at them coyly through her eyelashes. “Tiffany she kind of...pulled me down on top of her, right? And she’s...grinding against my leg so...I…” Eyes drifting away, a giggle snuck past Lydia’s lips. “I slipped my hand into her panties. And _fuck…_ ” Mouth falling open, Lydia exhaled audibly and Conan nearly lost his grip on his glass. “She was so damn wet.”

Large hand twitching at his hip, Bill’s voice came out even higher than usual. “Th-then what did you do?”

Taking half a step forward, Lydia locked into his sapphire eyes. “Then she let me get her naked…” Lydia was getting close, too close, but Bill didn’t know where to go, couldn’t move as her body swiveled into his. “And I spread her legs…” Tone low, sultry, Lydia tipped her lips up to Bill’s ear, but her eyes shifted to Conan as she reached out to encircle his wrist. “ _And I ate that pretty pussy until she screamed.”_

Shuddering, Bill let out a noise somewhere between a gasp and a whine as he folded against her, large hand grasping Lydia’s waist. Lassoing Conan in, Lydia fused their mouths together, burying her fingers in his orange hair while Bill tore down her spaghetti strap, his stubble chafing as he kissed over her shoulder.

For a moment they were an upstanding net of writhing need, Conan hiking up Lydia’s skirt, kneading her round ass as she palmed his stiff cock through his slacks while Bill ground into her leg, tugging down the collar of her dress and slipping his lengthy fingers into the cup of her bra to massage her breast.

“Fuck let’s, let’s…” Lydia breathed, head surfacing and glancing back towards the house. “Let’s go over there a little…okay?”

Bill and Conan hastily nodded, and like some sprawling six legged entity they continued to paw at each other as they moved into the shade of the trees, Lydia pushing Bill’s jacket from his vast shoulders as he finally exposed her chest, fondling her and tweaking a nipple between his thumb and forefinger while Conan groped her from behind. 

Long freckled fingers slithered into her panties as Conan brushed her hair away and kissed over Lydia’s neck. “Fuck, you’re so wet, Lyd…” Gliding his cock into the crack of her ass, Conan’s hand swiped past Bill’s as he passed over her abdomen and he locked into his deep blue eyes for half a moment before returning his attention to Lydia’s skin.

Hurriedly undoing Bill’s zipper, Lydia enveloped his thick cock and Bill moaned into her mouth. “I want to suck you so badly, Bill.”

Bill nodded insistently, sizable hand fisting in her scarlet tresses as he resisted the urge to pull her down. “Oh fuck. Yes. Now.”

Craning her neck, Lydia hooked an arm back to pull Conan closer. “Fuck me.”

“I don’t have a condom…” Conan peeled down her panties and stared into her glistening pink flesh, swallowing hard.

Lydia waved her hand. “I’m on the pill, it’s fine.” Inching Bill’s slacks down his thick thighs, Lydia hung on his shirt until he came to the ground with her, Bill kneeling as she lowered his boxers.

Lydia’s mouth encapsulated him and Bill’s eyes closed with a resounding groan. “Oh... _oh fuck_ …” 

Conan slid Lydia’s knees apart with one foot and dropped down, undoing his pants and clamping both massive hands around her hips. “Mmm…” Swiping his cock through the sopping folds of her pussy, Conan bent down to whisper in her ear, and at the last moment he flicked his crystalline eyes up to Bill. “You want to get fucked hard?”

Bill shivered as Lydia offered a muffled hum in the assent. Clapping against her ass, Conan sheathed himself to the hilt, curling an arm around to spin his fingers over Lydia’s clit as he began mercilessly pounding.

Conan’s vigorous thrusts forced Lydia forward, driving Bill’s substantial cock deep into her throat. “ _Oh...Oh Lydia, fuck! Your mouth! Fuck that feels so good!”_ Tossing his head back, Bill’s fingers danced over her scalp and he lost himself in the slippery suction until Conan’s grunt brought him back to the moment.

Oceanic eyes snapping open, Bill witnessed a side of Conan neither he, nor anyone, perhaps, had seen before. Blue eyes chips of ice, nose flaring, mouth a snarl, he planted one foot on the ground and hammered into Lydia viciously until she was screaming around Bill’s cock and struggling to maintain her focus. In that moment, Conan was nothing short of bestial and he looked from Bill, to Lydia’s head.

“Fuck her face.” Conan growled, hint of a smirk playing over his slender lips. “Do it.”

Breathing hard, Bill licked his pink lips, then combed back Lydia’s hair. “Lydia, can I…” Where Conan demanded effortlessly, Bill struggled to ask. “Could I..fuck your face? Is that okay?”

Lydia popped off for a moment, continuing to jerk him wildly. “ _Yes! Yes, please, Bill! Fuck! Fuck!”_ Her expression contorting as she tightened and shook around Conan’s hammering cock, Lydia nodded and took Bill back into her mouth when he aligned the wide head with her lips.

Tipping his pelvis forward hesitantly, Bill met Conan’s sea blue eyes. Conan nodded, egging him on and Bill bore in again, twisting his huge hands into Lydia’s auburn locks. 

“Yeah…” Conan bobbed his buoyant ginger hair, teeth bared. “Make her take it. Make her take your cock.”

Bill swiveled forward faster. “Like that?” Nose flaring, Bill gritted his teeth and the muscle in his sharp jaw flickered. “You like when I fuck her mouth? Hmm?” Fingertips digging into her scalp, Bill knit his dark eyebrows together and tilted his head. 

“Fuck...yeah…” Conan pummeled Lydia with an insane velocity, racing against her clit until she dripped over his fingers. “I love it. Fuck her throat, Bill. _Yes_.”

“ _Mmhmm…_ ” Lydia shrieked around his slamming cock and Bill fought to keep his gaze zeroed in on Conan as the moist, hot clutch of her grew overwhelming. “Yeah, fuck...fuck this feels so good…”

Conan chuckled. Actually chuckled, and Bill had no idea how he managed it with as hard as he was panting. “You gonna cum in her throat, Bill?” Conan sniffed, tossing back his tangerine hair. 

“Uh huh…” Scooting forward, Bill sat back on his heels, mountainous shoulders curled inward as he frantically humped Lydia’s face with high, desperate whimpers. “Can I? Can I, Lydia? I wanna cum in your mouth so bad. _Please? Fuck!”_

When she hummed and let him know that he could, Conan examined Bill’s face, a mask of lustful anguish as his body folded over and he tried to burrow impossibly deeper into Lydia’s recesses. “Do it…” Conan urged, hoping to catch a glimpse of Bill’s cobalt eyes one last time. “Do it, Bill. Cum in her throat. Cum. _Now_.”

Their blue eyes linked in the frozen second before a tumbling whine ripped from Bill’s firm chest and his powerful arms ensconced Lydia’s head. Hips leaping and left lid twitching, Bill’s hot, salty cum shot into the back of her throat and Lydia swallowed greedily before Bill let her go, crawling half a step away and covering his face with a trembling hand.

As Bill did up his pants, Conan removed himself long enough to flip Lydia over, mounting her with a smile. “Hey there.”

“Hey.” Lydia chuckled as Conan unceremoniously entered her, resuming his pace without fail and capturing her mouth. The residual taste of Bill lingered on her tongue and it spurred Conan on as Lydia’s hips rose to meet his every stroke. When she constricted around him again, her mouth unable to maintain their kisses, Conan lost count of how many times he made her cum beneath the leaves that night, but figured it didn’t matter as he slithered his lanky arms behind her back, crossing over her shoulders before he began rocketing forward.

“ _Oh Lyd! Yes! Fuck! You’re gonna make me cum so hard!_ ” If Conan was honest with himself, he thought about fucking Lydia during the course of their friendship. More than once. So to finally get the opportunity was exhilarating as he swooped into her neck to nip at her dewy skin. 

“You gonna let me cum inside you, huh?” Conan murmured against her ear. “Let me cum in this tight pussy? Is that what you want Lyd? _Huh?”_

Ripping at his ginger tresses, Lydia’s screaming scared the birds from the trees. “ _Yes! Conan, fuck! I want your cum so bad! Fuck! Don’t stop! Yes! Fuck! FUCK!_ ” Squeezing him again, Conan molded against her, a deep, guttural groan escaping him before he tensed. Yanking Lydia’s body down onto himself, Conan let out several dusky huffs, eyes squinched and mouth agape.

“ _Fuck! Yes! Lyd! Fuck!”_ Cum blooming inside of her, Conan collapsed, chest heaving as Lydia’s limbs wrapped around him and she rocked them back and forth for a moment. 

Bill timidly snuck up to them, interlacing his fingers with Lydia’s once she dropped an arm. Smiling up at him, Lydia motioned for Bill to come down and fused their mouths together, a patient, gentle kiss passing between them before she scratched under Bill’s square chin and he grinned.

As Conan started to rise, Lydia gave him a meaningful look, then moved her eyes over to Bill. Raising his pale eyebrows, Conan smirked, removing himself from her and sitting back. Then, staring hard at Bill, Conan slowly let his eyes fall between Lydia’s legs.

Bill glanced between them and noticed the sticky white liquid dribbling out, lifting his eyes back to Conan, who tightened his jaw and gave him a heavy nod.

Lying between Lydia’s legs, Bill’s pink lips brushed over her thighs, touched a kiss to her hood, poised himself above her slit and waited for her to smile down at him and run her fingers through his chestnut locks before licking her open with his long tongue.

Bill inhaled Conan’s cum, salinic and warm, cleaning Lydia effectively and pleasurably before he felt a tapping on his shoulder. Two of Conan’s freckled fingers beckoned him and Bill rose. Large hand hooking over the back of his neck, Conan dragged him forward, latching onto Bill’s mouth and opening his lips, tongue twirling inside until they shared his essence. Conan’s fingers tugged at his hair as he hummed in satisfaction, parting from Bill with a nod and a swallow before patting his rough cheek.

The three of them stood, putting themselves back together. “Well…” Conan replaced the sleeve of Lydia’s dress and pulled a twig from her hair then, taking in Bill’s appearance, narrowed his eyes, pursed his lips, and smiled to himself. “Good party.” Smacking Bill’s tiny ass and leaving him blinking in amusement, Conan held a hand aloft in farewell, Lydia laughing as his tall figure retreated into the darkness.

**Author's Note:**

> Thank you for taking the time to read. If you enjoyed this story, please leave a comment or come say hi on tumblr at fandomtransmandom. I also take requests!


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